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HomeProduct name listBROMOPRIDE

BROMOPRIDE

  • CAS NO.:4093-35-0
  • Empirical Formula: C14H22BrN3O2
  • Molecular Weight: 344.25
  • MDL number: MFCD00078959
  • EINECS: 223-842-2
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-19 20:33:22
BROMOPRIDE Structural

What is BROMOPRIDE?

Description

Bromopride is a dopamine D2 receptor antagonist (Ki = 14 nM). It binds to bovine anterior pituitary membranes with an IC50 value of 2.13 μM. Bromopride inhibits cholinesterase activity in vitro in rat plasma and striatum homogenate (IC50s = 67.8 and 38.4 μM, respectively). It increases serum prolactin levels in rats by 100% when used at a dose of 0.02 mol/kg. Bromopride (2.5 mg/kg) decreases locomotion and rearing in an open field test and impairs acquistion, but not retention, of a conditioned avoidance response in a two-way active conditioned avoidance test in rats.

Chemical properties

White Solid

Originator

Praiden,Italchemi,Italy,1977

The Uses of BROMOPRIDE

An antiemetic.Bromopride is used in method and a system for analyzing neuropharmacology of a drug.

What are the applications of Application

Bromopride is an antiemetic agent that acts as a D2DR (dopamine D2 receptor) antagonist

Definition

ChEBI: 4-amino-5-bromo-N-[2-(diethylamino)ethyl]-2-methoxybenzamide is a member of benzamides.

Manufacturing Process

To 119 g (0.45 mol) of N-(2-diethylaminoethyl)-2-methoxy-4-aminobenzamide dissolved in 200 cc of acetic acid are added in the cold in small portions 69 g of acetic anhydride (0.45 mol + 50% excess). The starting material is made by esterifying 4-aminosalicylic acid with methanol, then acetylating with acetic anhydride and then methylating with dimethyl sulfate. The solution obtained is heated for 2 hours on a water bath and then boiled for 15 minutes. It is cooled at 25°C. While agitating constantly and maintaining the temperature between 25° and 30°C, there is added to the solution drop by drop 72 g of bromine dissolved in 60 cc of acetic acid. It is agitated for one hour. The mixture obtained is added to one liter of water and the base is precipitated by the addition of 30% soda, The precipitated base is extracted with 40 cc of methylene chloride. After evaporation of the solvent, the residue is boiled for two hours with 390 g of concentrated hydrochloric acid in 780 cc of water. It is cooled, diluted with one liter of water, 12 g of charcoal are added, and the mixture filtered. The base is precipitated with 30% soda. The N-(2- diethylaminoethyl)-2-methoxy-4-amino-5-bromobenzamide formed crystallizes, is centrifuged and washed with water. A yield of 85 g of base having a melting point of 129°-130°C is obtained.
To produce the dihydrochloride, the free base is dissolved in 110 cc of absolute alcohol, 9.6 g of dry hydrochloric acid dissolved in 35 cc of alcohol are added, followed by 2.8 cc of water. The dihydrochloride precipitates, is centrifuged, washed, and dried at 40°C. It was a solid white material having a melting point of 134°-135°C.

Therapeutic Function

Antiemetic

Properties of BROMOPRIDE

Melting point: 148-150?C
Boiling point: 435.8±45.0 °C(Predicted)
Density  1.4132 (rough estimate)
refractive index  1.6200 (estimate)
storage temp.  2-8°C
solubility  Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
form  Solid
pka 13.84±0.46(Predicted)
color  White to Off-White

Safety information for BROMOPRIDE

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H302:Acute toxicity,oral
H312:Acute toxicity,dermal
H332:Acute toxicity,inhalation
Precautionary Statement Codes P280:Wear protective gloves/protective clothing/eye protection/face protection.

Computed Descriptors for BROMOPRIDE

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